Penn's first modeling billboards were for Gap in 2013.[16] Then she appeared in GQ in December 2013,[17] in W in January 2014,[18] and Elle in March 2014.[15]

Penn posed for photographer Tony Duran for a partially nude cover and an interior layout in the seventh issue of the erotica and fine arts magazine treats!, released in April 2014.[19] Penn said that she had "always loved [Duran's] black-and-white nudes".[11] Within weeks of the issue's release, Penn signed a new modeling contract with Premier Model Management to represent her in the United Kingdom.[16][20]

Her first film was the horror movie Condemned, directed by Eli Morgan Gesner, in which she plays the girlfriend of a band member living in a rundown building[31][32] The film opened on Friday the 13th in November 2015.[33] Another early role was in Elvis & Nixon, which stars Kevin Spacey.[34] The movie was presented in at least one spring film festival and was released in April 2016.[35][36] In November 2015 it was announced that she had booked roles in a pair of independent films: GenRX and Unfiltered.[37]